I've been trying to write a post for months and months about how to compliment someone with chronically low self-esteem, but honestly its so damn giver and recipient specific that its kind of pointless. Still. Here's my best shot at a guide. If nothing else, take it as moderately accurate for complimenting me. (not that you ever should)
Be genuine. Dead serious if you ever tell a white lie and it gets found out, your credibility is fucked. you're already on thin ice by complimenting a girl that has dogshit self-esteem. She already thinks you're lying. Don't prove her right.
Be specific. "I like X" is meh. "I like X, particularly because of Y and Z" is better. Prove that you've put thought into it, that you're coming to your opinion from a rational, reasoned-out space.
Be critical. This one is a bit dicey because it's not always true, but SOMETIMES, a bit of brutal honesty mixed in with genuine compliments can make them work better. It runs of the risk of ruining everything you're trying to say, though.
Be targeted. Let's get a bit wordy here. People have narratives about themselves, things they take pride in, and build their identity around. Some people think of themselves as successful, some people think of themselves as artists, as kinksters. If you can identify what people take pride in about themselves and compliment that, you have a much better chance of getting a critical hit.
Be cautious. Hey. Do not. Compliment something you don't know anything about. If you don't know what she looks like, don't even comment on her appearance. If you know she's insecure about something, unless you're VERY close, don't bring it up. Imagine yourself navigating a fucking minefield if you have to. Don't be weird.
Be affirming. This one is tricky, because you have to gauge your distance carefully. "I'm glad you're alive" from a complete stranger sucks ass and feels fake. A more targeted appreciation of "Your writing makes me feel X,Y,Z" can be really nice, though, and can make a general affirmation land! I don't know just... look. Sometimes, people wonder if they'd be better off dead. The goal here is to remind them that that's not true.
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